Tag: M.W=200-300

Electric Literature of 645-00-1, A common heterocyclic compound, 645-00-1, name is 1-Iodo-3-nitrobenzene, molecular formula is C6H4INO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a mixture of 3-iodonitrobenzene (7 g, 28.1 mmoles), K2CO3 (11.63 g, 84.3 mmoles) in 80 mL 1,2-DME/water (1: 1) were added successively CuI (229.50 mg, 1.21 mmoles), PPH3 (591.20 mg, 2.25 mmoles), Pd/C 10% (598. 0 mg, 0.562 mmoles). The mixture was stirred at room temperature for 1 hour. 4-BUTYN-1-OL (5.90 g, 84.30 mmoles) was added, then the mixture was heated to reflux overnight. After cooling, the mixture was filtered on Celite and the organic layer was evaporated under reduced pressure. Tha aqueous layer was acidified with concentrated Chlorhydric acid and extracted with AcOEt. The organic layer were washed with brine, dried, filtered and evaporated. Purified by flash CHNNATOGRAPHY on silica gel AcOEt/Hexanes (35: 65). Yield: 81% H NMR (CDC13,300 MHz) 8 : 8.29 (s, Ar, 1H), 8.17 (M, Ar, 1H), 7.74 (d, Ar, 1H, J = 8HZ), 7.51 (t, Ar, 1H, J = 8Hz), 4.53 (d, 2H, J = 6Hz). A mixture of 3-(3-nitrophenyl)-prop-2-yn-1-ol (100 mg, 0.564 mmoles), Pd/C 10% (10 mg, 0.094 mmoles) was hydrogenated under 38 psi overnight. The mixture was filtered on Celite and the filtrate was evaporated to dryness. Purified by flash chrmatography on silica gel AcOEt/Hexanes (25: 75). Yield: 99% H NMR (CDC13, 300 MHz) 8 : 7.08 (t, Ar, 1H, J = 8. 0Hz), 6.61 (d, Ar, 1H, J = 7. 5HZ), 6.53 (M, Ar, 2H), 3.67 (t, 2H, J = 6. 5HZ), 2.84 (s, 3H), 2.62 (t, 2H, J = 8. 0Hz), 1.87 (M, 2H). 3-(3-aminophenyl)propan-1-ol was then reacted with 2-chloroethylisocyanate as described in examples 1-12 to obtain desired product. Purified by flash chromatography on silica gel ETOH/CH2CL2 (2: 98).EXAMPLE 45: Preparation of Acetic acid 3- {3- [3- (2-CHLORO-ETHYL)-UREIDO]-PHENYL}-PROPYL ester (42) To a mixture OF 3-IODONITROBENZENE (1 g, 4.56 mmoles), K2CO3 (1.57 g, 11.4 mmoles) in 30 mL 1.2-DME/water (1: 1) were added successively CuI (34.78 mg, 0. 18 mmoles), PPH3 (95.80 mg, 0.36 mmoles), Pd/C 10% (97.05 mg, 0.09 mmoles). The mixture was stirred at room temperature for 1 hour. Propargyl alcohol (807 mg, 14.40 mmoles) was added, then the mixture was heated to reflux overnight. After cooling, the mixture was filtered on Celite and the organic layer was evaporated under reduced pressure. Tha aqueous layer was acidified with concentrated Chlorhydric acid and extracted with AcOEt. The combined organic layers were washed with brine, dried, filtered and evaporated. Purified by flash chromatography on silica gel CH2CL2/ETOH (95: 5). Yield: 81% IH NMR (CDC13, 300 MHz) 8 : 8.29 (s, Ar, 1H), 8.17 (M, Ar, 1H), 7.74 (d, Ar, 1H, J = 8HZ), 7.51 (t, Ar, 1H, J = 8Hz), 4.53 (d, 2H, J = 6Hz). To an ice-cold 3- (3-NITROPHENYL)-PROP-2-YN-L-OL (150 mg, 0.85 mmoles) in diethylether (10 mL) were added acetic anhydride (254.23 mg, 2.54 mmoles), triethylamine (256.54 mg, 2.54 mmoles), 4-pyrrolidinopyridine (2.52 mg, 0.017 mmoles) and the mixture was stirred at room temperature for 12 hours. The reaction was quenched by saturated solution OF NA2C03 and the mixture was extracted with AcOEt. The extracts were washed with brine, dried and evaporated. Purified by flash chromatography on silica gel AcOEt/Hexanes (8 : 2). Yield: 99% IH NMR (CDC13, 300 MHz) 8 : 8.24 (s, Ar, 1H), 8.14 (d, Ar, 1H, J = 8. 5HZ), 7.71 (d, Ar, 1H, J = 7. 5HZ), 7. 48 (t, Ar, 1H, J= 8HZ), 4. 88 (s, 2H), 2.12 (s, 3H). A mixture of acetic acid 3- (3-NITROPHENYL)-PROP-2-YNYL ester (100 mg, 0.48 mmoles), Pd/C 10% (10 mg, 0.094 mmoles) in 30 mL of dry ethanol was hydrogenated under 38 psi overnight. The mixture was filtered on Celite and the filtrate was evaporated to dryness. Purified by flash chromatography on silica gel AcOEt/Hexanes (25: 75). Yield: 81% IH NMR (CDC13,300 MHz) 8 : 7.08 (m, Ar, 1H), 6.59 (d, Ar, 1H, J = 7. 5HZ), 6.53 (m, Ar, 2H), 4.09 (t, 2H, J = 6. 5HZ), 3.66 (s, 2H), 2.60 (t, 2H, J = 8HZ), 2.06 (s, 3H), 1.93 (M, 2H). Acetic acid 3- (3-AMINOPHENYL)-PROP-2-YNYL ester was then reacted with 2-chloroethylisocyanate as described in examples 1-12 to obtain desired product. Purified by flash chromatography on silica gel ACOET/CH2CL2 (2: 8). Yield: 93%

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; IMOTEP INC.; WO2004/106291; (2004); A1;,
Iodide – Wikipedia,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 25309-64-2, name is 1-Ethyl-4-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 25309-64-2

13.20 g (31.64 mmol) of 1-benzyl-4-(benzyloxy)-3-iodopyridin-2(1H)-one are, together with 26.4 ml of triethylamine, initially charged in 224 ml of acetonitrile. 1.11 g (1.58 mmol) of bis(triphenylphosphine)palladium(II) chloride, 301 mg (1.58 mmol) of copper(I) iodide and 4.20 g (41.13 mmol) of ethynylbenzene are added, and the mixture is, under argon and with stirring, heated at 60 C. for 22 h. The mixture is then allowed to cool to room temperature, 11.01 g (47.45 mmol) of 4-ethyliodobenzene are added and the mixture is once more, under argon and with stirring, heated at 60 C. for 24 h. The mixture is then concentrated and filtered through silica gel (mobile phase: cyclohexane/ethyl acetate 1:1, then dichloromethane/methanol 95:5). The product-containing fractions are combined and concentrated. The product obtained in this manner is once more purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol 100:3). The product-containing fractions are once more combined and concentrated. The residue is dissolved in warm ethyl acetate, a little activated carbon is added, the mixture is briefly heated to the boil and the activated carbon is filtered off again. After cooling to room temperature, the precipitated crystals are filtered off with suction, and more crystals are obtained from the mother liquor. In this manner, a total of 6.00 g (44.1% of theory) of the target compound are obtained.LC-MS (method 1): Rt=2.86 min; m/z=406 (M+H)+ 1H-NMR (400 MHz, CDCl3): delta=7.85 (d, 1H), 7.49-7.23 (m, 11H), 7.22 (d, 2H), 6.05 (d, 1H), 5.45 (s, 2H), 2.69-2.61 (q, 2H), 1.26-1.21 (t, 3H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 25309-64-2.

Reference:
Patent; Lampe, Thomas; Kast, Raimund; Beck, Hartmut; Stoll, Friederike; Becker, Eva-Maria; Jeske, Mario; Schuhmacher, Joachim; US2010/261736; (2010); A1;,
Iodide – Wikipedia,
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Related Products of 2265-93-2, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2265-93-2, name is 2,4-Difluoroiodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Synthesis of (2,4-difluorophenyl)propiolic Acid 4.95 ml (41.4 mmol) of 2,4-difluoroiodobenzene and 2.56 ml (41.4 mmol) of propiolic acid were dissolved in DMF (16 ml). Following cooling of the reaction medium to 0 C. (ice-water bath), 578 mg (0.83 mmol) of Pd(PPh3)2Cl2 and 308 mg (1.66 mmol) of Cul were added. The reaction solution was then cooled to -10 C. (ice methanol bath) and 14.5 ml (103.4 mmol) of diisopropylamine were added dropwise at this temperature. The cooling bath was then removed and the reaction mixture was stirred a further 16 h after RT had been re-established. The reaction solution was then diluted with EA and washed successively with a 2N HCl solution and a satd aq. NaCl solution. Following drying over MgSO4, filtration, and removal of solvent in vacuo, the residue was boiled with hexane and filtered after cooling to RT. The residue was dissolved in diethyl ether at 30 C. and filtered at this temperature. By removal of solvent in vacuo there were obtained from the filtrate 6.43 g (35.3 mmol, 85%) of (2,4-difluorophenyl)propiolic acid.

The synthetic route of 2,4-Difluoroiodobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gruenenthal GmbH; US2007/112011; (2007); A1;,
Iodide – Wikipedia,
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Synthetic Route of 645-00-1,Some common heterocyclic compound, 645-00-1, name is 1-Iodo-3-nitrobenzene, molecular formula is C6H4INO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: In a typical method, 1 mmol of bromobenzene, 1 mmol of methylacrylate, 0.04 g of PdNPsPANI/silica-HNS, and 2 mmol of Et3N wereadded to 5 mL of DMF:H2O (1:1) and allowed to stirrer at 130 C. Thereaction completion was monitored by TLC (n-hexane and ethyl acetatemixture as solvent-5:1). After completion of the reaction, the reactionwas cooled to room temperature, the catalyst was removed by filtration.The catalyst was then washed with Et2O (3 5 mL). The organic layerwas separated and dried over anhydrous Na2SO4. The solvent wasevaporated under reduced pressure to give the corresponding arylolefins.To optimize the reaction conditions, GC was used to investigatethe yields under each condition. The NMR spectroscopic data of known compounds were found to be identical with those reported in the literature.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Iodo-3-nitrobenzene, its application will become more common.

Reference:
Article; Rostamnia, Sadegh; Kholdi, Saba; Journal of Physics and Chemistry of Solids; vol. 111; (2017); p. 47 – 53;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 58313-23-8, name is Ethyl-3-iodobenzoate, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 58313-23-8, Quality Control of Ethyl-3-iodobenzoate

General procedure: Hydrazide ligands (1-12) were synthesized by reportedmethod [28,29]. Ethylbenzoate (25 mmol) was dissolved inethanol (75 mL), and then hydrazine hydrate (100 mmol)was added and the mixture refluxed for 5 h. The solid obtainedwas washed with hexane to afford the hydrazide.Other ligands were prepared from their respective esters. Theanalytical data of benzohydrazide (1), M.P. 116 C; 2-fluorobenzohydrazide (2), M.P. 74 C; 2-methoxybenzohydrazide(3), M.P. 83 C; 2-aminobenzohydrazide (4), M.P.124 C; 4-phenylsemicarbazide (5), M.P. 125 C; 3-aminobenzohydrazide(6), M.P. 79C; 4-aminobenzohydrazide (7),M.P. 229 C; 3-methoxybenzohydrazide (8), M.P. 94 C; 3-fluorobenzohydrazide (9), M.P. 138 C; 3-iodobenzohydrazide(10), M.P. 141 C; 4-iodobenzohydrazide (11) M.P.170 C and 3-bromobenzohydrazide (12) M.P. 160 C; werereported previously [28,30].

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Shamshad, Bushra; Jamal, Rifat A.; Ashiqa, Uzma; Mahrooof-Tahirb, Mohammad; Shaikha, Zara; Sultana, Sadaf; Khanc, Khalid M.; Medicinal Chemistry; vol. 11; 8; (2015); p. 798 – 806;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 608-28-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 608-28-6 name is 2-Iodo-1,3-dimethylbenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: Under nitrogen atmosphere, Cu2O (10 mol %), DABCO (25 mol %), and a stirring bar were added into a 10 mL oven-dried sealed glass tube (as shown in Figure S1). Then NMP (0.5 mL), aryl iodides (0.125 mmol, 1.0 equiv.) and PhSiH3 (0.75 mmol, 6 equiv.) were injected by syringe. The tube was then sealed and CO2 (0.67 mmol, 5.4 equiv., 15 mL) as well as NH3 (0.67 mmol, 5.4 equiv., 15 mL) were injected by syringe after N2 was removed under vacuum. Finally, the mixture was stirred for 24 hr in a pre-heated-to-130 C alloyed block. After the reaction was finished, the tube was cooled to room temperature and the pressure was carefully released. The yield of were measured by GC analysis using dodecane as the internal standard or by flash chromatography on silica gel (petroleumether/ethyl acetate).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Iodo-1,3-dimethylbenzene, and friends who are interested can also refer to it.

Reference:
Article; Wang, Hua; Dong, Yanan; Zheng, Chaonan; Sandoval, Christian A.; Wang, Xue; Makha, Mohamed; Li, Yuehui; Chem; vol. 4; 12; (2018); p. 2883 – 2893;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 16932-44-8, name is 2-Iodo-1,3-dimethoxybenzene, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 16932-44-8, category: iodides-buliding-blocks

General procedure: For a typical reaction, a Vapourtec 2R+ Series was used as the platform with a Vapourtec Gas/Liquid Membrane Reactor to load the carbon monoxide. The HPLC pump were both set at 0.125 mL/min, temperature of the reactor at 110 C, pressure of CO at 15 bar with a back pressure regulator of 250 psi (17.24 bar). The system was left running for 2 h to reach steady state after which time the flow streams were switched to pass from the loops where the substrates and catalysts were loaded. The first loop (5 mL) was filled with a solution of palladium acetate (20 mg, 0.08 mmol), triphenylphosphine (48 mg, 0.168 mmol) in 6 mL of 1,4-dioxane while the second loop (5 mL) was filled with a solution made from the ortho-substituted iodoarene substrate (1.68 mmol), triethylamine (0.272 g, 0.374 mL, 2.69 mmol) and water (0.505 g, 28 mmol) in 5.8 mL of 1,4-dioxane. An Omnifit column filled with 1.71 cm3 (r = 0.33 cm, h = 5.00 cm) of cotton was positioned just before the back pressure regulator to trap any particulate matter formed to avoid blocking of the back pressure regulator. After the substrates were passed through the system, the outlet of the flow stream was directed into a receptacle where the excess carbon monoxide gas was vented off in the fume cupboard. The reaction mixture was then evaporated to dryness, ethyl acetate (25 mL) and sodium carbonate solution (2 M, 10 mL) were added and transferred to a separating funnel. After collecting the aqueous layer, the organic layer was extracted with sodium carbonate solution (2 M, 2 × 10 mL). The combined aqueous layers were acidified by the addition of 2 M HCl solution which was then extracted with ethyl acetate (3 x 25 mL). The organic layer was dried over sodium sulfate, and the solvent evaporated under vacuum to give the crude product as a solid. The crude product was then recrystallised from the appropriate solvent.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Mallia, Carl J.; Walter, Gary C.; Baxendale, Ian R.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 1503 – 1511;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 13194-68-8, A common heterocyclic compound, 13194-68-8, name is 4-Iodo-2-methylaniline, molecular formula is C7H8IN, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A mixture of CuCl (5 g, 50.5 mmol) and pyridine (50 mL) was stirred at r.t. for 30 min. The suspension was filtered and the halogenated aniline (1.5 equiv) was added to the green solution. Air was bubbled through the solution for 18 h. The residue was diluted with CH2Cl2 (200 mL) and aq 1 M HCl (100 mL). The aqueous layer was extracted with CH2Cl2 (3 × 100 mL). The combined organic layers were washed with H2O (100 mL), dried (MgSO4), and concentrated.The crude product was recrystallized from EtOH.

The synthetic route of 13194-68-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Koehl, Isabel; Luening, Ulrich; Synthesis; vol. 46; 17; (2014); p. 2376 – 2382;,
Iodide – Wikipedia,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 214279-40-0, name is 2-Iodo-4-methoxy-1-nitrobenzene, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2-Iodo-4-methoxy-1-nitrobenzene

To a solution of 3-iodo-4-nitroanisole (2.79 g, 10.0 mmol) in anhydrous THF (10 mL) at minus 40C under a nitrogen atmosphere, phenylmagnesium chloride (2 M in THF, 4.2 mL, 8.3 mmol) was added dropwise at a rate such that the temperature would not exceed minus 35C. Upon completion of the addition, the mixture was stirred at minus 40C for two hours, followed by addition of trimethylacetaldehyde (1.1 mL, 10 mmol). The mixture was stirred at minus 40C for two hours and then at room temperature for another one hour. The reaction was then quenched with brine (100 mL), and the mixture was extracted with CH2CI2 (40 mL) three times. The combined organic phase was dried over Na2S04, concentrated in vacuo, and the residue was purified by silica gel column chromatography to yield racemic (R/S)-l -(5-methoxy-2-nitrophenyl)-2,2-dimethyl- l-propanol (1.76 g, 88%). 1H NMR (400 MHz, CDCk): delta 7.89 (d, 1 H, J = 9.2 Hz, Ph-H), 7.27 (d, 1 H, J = 2.8 Hz, Ph-H), 6.84 (dd, 1 H, J= 8.8 and 2.8 Hz, Ph-H), 5.62 (d, 1 H, J= 4.0 Hz, PhCH), 3.89 (s, 3 H, OCH3), 2.08 (d, 1 H, J= 4.0 Hz, OH), 0.89 (s, 9 H, C(CH3)3).

According to the analysis of related databases, 214279-40-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LASERGEN, INC.; STUPI, Brian, Philip; LI, Hong; WU, Weidong; HERSH, Megan, N.; HERTZOG, David; MORRIS, Sidney, E.; METZKER, Michael, L.; WO2013/40257; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 101066-87-9, name is 4-Iodo-2-(trifluoromethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Iodo-2-(trifluoromethyl)benzonitrile

A suspension of frans-1-(4-methoxybenzyl)hexahydropyrano [3,4-cfl imidazol-2(3/-/)-one [racemic (±)] (0.25 g, 0.95 mmol), 4-iodo-2-(trifluoromethyl)benzonitrile (0.28 g, 0.95 mmol), frans-A/,A/’-dimethylcyclohexane-1 ,2-diamine (0.032 g, 0.29 mmol) and potassium carbonate (0.395 g, 2.86 mmol) in toluene (15 ml_) was degassed for 30 min in a microwave vial. Cul (0.009 g, 0.05 mmol) was added and the vial was sealed with an aluminum cap. The sealed vial was kept in a preheated oil bath at 1 10 C and stirred for 12 h. The reaction mixture was cooled to RT, filtered through a pad of celite, and filtrates were concentrated under reduced pressure to give a black residue. The residue was purified by column chromatography on silica gel (dichloromethane/methanol = 100:0 to 99: 1 ) to give the title compound (0.17 g, 41.0%) as an off white solid. LCMS: m/z 432.1 [M+H]+; H NMR (400 MHz, CDCI3) delta 7.80-7.74 (m, 2H), 7.54 (d, 1 H), 7.20 (d, 2H), 6.84 (d, 2H), 4.50 (d, 1 H), 4.40-4.30 (m, 2H), 4.15-4.05 (m, 1 H), 3.80 (s, 3H), 3.65 (ddd, 1 H), 3.50-3.20 (m, 2H), 3.10 (ddd, 1 H), 1.90 (d, 1 H), 1 .72-1.68 (m, 1 H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 101066-87-9.

Reference:
Patent; NOVARTIS AG; BOCK, Mark; CHIKKANNA, Dinesh; GERSPACHER, Marc; KHAIRNAR, Vinayak; LAGU, Bharat; PANDIT, Chetan; WO2013/84138; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com